Ullmann homocoupling of arenediazonium salts in a deep eutectic solvent. Synthetic and mechanistic aspects

Ghigo, Giovanni; Bonomo, Matteo; Antenucci, Achille; Damin, Alessandro; Dughera, Stefano

doi:10.1039/d2ra05272e

Cited by 6 publications

(3 citation statements)

References 56 publications

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“…Therefore, we tested three different DESs (Figure 1), formed by, respectively: glycerol as hydrogen bond donor (HBD) and choline acetate as HBA (DES1); [14d] urea as HBD and choline nitrate as HBA (DES2); [14d] glycerol as HBD and KF as HBA (DES3) [16a,c] . The results are summarized in Table 2.…”

Section: Resultsmentioning

confidence: 99%

“…Interestingly, they have also proved to be excellent solvents in the main cross‐coupling reactions [15] . In our previous researches, DESs or DES‐like mixtures, based on glycerol and different halide organic and inorganic salts, were successfully exploited as new media in three reactions of arenediazonium tetrafluoroborate (Scheme 2), namely metal‐free hydrodediazoniation (reaction 1), [16a] copper‐free halodediazoniation (reaction 2) [16b] and Ullmann homocoupling (reaction 3) [16c] …”

Section: Introductionmentioning

confidence: 99%

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Cross‐Coupling Reactions between Arenediazonium o‐Benzenedisulfonimides and Organolithium Reagents in a Deep Eutectic Solvent

Antenucci,

Dughera

2023

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A deep eutectic solvent (DES) based on glycerol and KF is successfully exploited as a solvent medium in cross‐coupling reactions between arenediazonium o‐benzenedisulfonimides and organolithium reagents (Muharashi‐Feringa coupling). The reactions were carried out in open air and in mild conditions. The target products were obtained in fairly good yield (15 examples; average yield: 60 %). This is, on the best of our knowledge, the first example of Muharashi‐Feringa coupling carried out with diazonium salts. A tentative hypothesis of the reaction mechanism was also proposed.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cross‐Coupling Reactions between Arenediazonium o‐Benzenedisulfonimides and Organolithium Reagents in a Deep Eutectic Solvent

Antenucci,

Dughera

2023

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“…We decide to explore the reactivity of benzyl chloride 4 with n -BuLi in different DESs ( Table 2 ), including the eutectic mixture Gly:KF 6:1 ( Table 2 , entry 4), recently designed and exploited by some of us [ 44 , 45 , 46 ].…”

Section: Resultsmentioning

confidence: 99%

Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry

et al. 2022

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A chiral glycerol derivative, namely 3-amino-1,2-propanediol, was employed for as the hydrogen bond donor (HBD) in the design of a new deep eutectic solvent (DES) with choline chloride acting as the hydrogen bond acceptor (HBA). The novel mixture was characterized and unambiguously classified as a DES. Furthermore, its synthetic usefulness was demonstrated in the room-temperature n-butyllithium-addition under air to carbonyl compounds and benzyl chloride. In some cases, pure products (100% conversion) were obtained by a simple extractive work-up in up to 72% isolated yield, thus suggesting the potential practical usefulness of this procedure as a green alternative to the classical Schenk procedure in volatile organic solvents for the synthesis of tertiary alcohols. The chirality of the HBD, bearing an interesting basic primary amino group, is an intriguing feature currently under investigation for further exploitation.

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Application of Deep Eutectic Solvents in Formation of Carbon‐Carbon and Carbon‐Heteroatom Bond by Cross‐Coupling Reactions

Jiang,

Wu,

Zhong

et al. 2023

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Deep eutectic solvents (DESs), known as the emerging organic reaction medium in the 21st century, have many advantages such as cheap, readily available, non‐pollution, and biodegradable. Its good properties make it an alternative to volatile organic solvents. The insights in to carbon‐carbon and carbon‐heteroatom bond formations and their applications since 2017 are encapsulated, which not only highlighting the significant achievements pertaining to the important role of DESs as solvents but also including popular named organic reactions for cross‐coupling reactions relating to the nature of DESs and the core optimum conditions. The review also encompasses a brief overview of the current situation and future development of DESs.

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Ullmann homocoupling of arenediazonium salts in a deep eutectic solvent. Synthetic and mechanistic aspects

Abstract: DES is exploited as a solvent media in Ullmann homocoupling of arenediazonium salts. Computational study supported by Raman spectroscopy is presented, aiming to elucidate the reaction mechanism.

Cited by 6 publications

References 56 publications

Cross‐Coupling Reactions between Arenediazonium o‐Benzenedisulfonimides and Organolithium Reagents in a Deep Eutectic Solvent

Cross‐Coupling Reactions between Arenediazonium o‐Benzenedisulfonimides and Organolithium Reagents in a Deep Eutectic Solvent

Design of a New Chiral Deep Eutectic Solvent Based on 3-Amino-1,2-propanediol and Its Application in Organolithium Chemistry

Application of Deep Eutectic Solvents in Formation of Carbon‐Carbon and Carbon‐Heteroatom Bond by Cross‐Coupling Reactions

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